Finding the Perfect Fit Pt. 07

Tuesday Night

Making it to Tuesday was annoying but Jamie confirmed he was still coming over, despite work trying to steal him away. Classes wore on and on, the clock mocking me as minutes steadily grew longer. I made it though!

After class, I went looking for food, hoping to calm down after the annoying day I'd just had. Getting off campus, I thought about Jamie coming over tonight and instead of going towards where all the restaurants were, instead I drove to Wal-Mart. I could pick up something to eat there but I was more interested in what I had remembered.

During our time together, I had wished Jamie had some conditioner and chap stick and with that thought now back, I wasn't letting it go. Even with it being bastard cold out, there were still plenty of people clogging up the store. Without Jamie, this trip would be easier than the last one and just as quick. That was until I walked past the make up section and the heat that Jamie was always able to summon flared back up, making demands that seemed quite reasonable at the time.

I swear I just meant to grab some lip gloss but that was right beside the lip stick and oh fuck, eyeliner was close by and what would Jamie look like with eye shadow? By the time I left, I had hair clips and ties along with conditioner, the previously mentioned make up, chap stick, a choker necklace for reasons, a bottle of tingling mint scented lube and a box of condoms. Those last two had been somewhat near the shower supplies and well, why not? I'd spent more than expected but I walked out of there happy, head buzzing with ideas.

It was on my drive home that I remembered that I was hungry, my stomach having taken a backseat to being horny. I got a burger at a drive through and headed home, it growing darker and colder as afternoon started giving way to dusk. Got home without incident, the radio playing some catchy song I didn't know before giving way to commercials that made me switch it off. Once inside, I ate while looking over what I had bought. Donna wasn't home, making this the perfect time for Jamie to come over.

I sent a text to him while playing with the tiny bottle of lube, not sure how tonight was going to play out. I'd gotten this on impulse, along with the rubbers, happily shopping and not thinking it through. Jamie said he was a virgin the night I first kissed him. Did he feel like giving his first time to me? Dare I even ask? He was coming over to try on clothes, not to fuck. Right?

Grabbing the condoms and lube, I threw them under the bed. It was a weekday night, I had class in the morning and work after, now wasn't the time. Outta sight, outta mind.

I heard something familiar but faint, me leaving my room and hearing a knock coming from the front door. Opening it revealed a bundled up Jamie, hands in pockets, face red from the cold instead of the usual way I was used to.

"You walked?! I could have given you a ride!" I stood aside as he came in, shutting and locking out the cold.

"Had some things on my mind. And it's not the first time I've walked in the cold." Unzipping his coat, he removed earbuds and tucked them away as I tried to figure out what to say to that. What would he think if I told him the stuff was waiting, we could go in my room and fuck? Instead I kept my mouth shut and followed Jamie, shutting my bedroom door as Jamie took his coat off, the usual hoodie under it. Walking over to my desk, I pulled out the bag from two nights ago and brought it over to my bed as I sat, warming up to the idea of Jamie getting to try on his new clothes. In the bag was the empty package that held the panties Jamie had taken with him and a warm bloom of heat returned as I remembered the picture he had sent.

"They fit alright?" Jamie's face lit up red, eyes flicking towards the floor before meeting mine, biting his lower lip as a smile struggled to surface. Molten lust screamed to life as he brushed hair out of his face, looking more like a girl now than ever before. That smile, with his head tilted slight to the side and color in his cheeks, was going to kill me. He was bashful yet eager, tender yet proud and everything I hadn't known I wanted.

"Yeah, just takes some getting used to." Pulling his hoodie off, Jamie tossed it aside before undoing the button on his jeans. Sitting there, unable to look away this time, I watched his pants drop into a puddle of denim about his ankles. Sure, it was just a pair of plain black panties but they failed to hide his obvious excitement at either wearing or showing them off.

"How do they fit in the back?" I asked, not sure where that question had come from but glad I'd said it. With color burning in his face, Jamie turned to the side, pulling up his shirt so I could get a clear look. His bare legs were on display but that was an afterthought as I looked at his butt, admiring the shape from the side then back as he turned. Reaching, he grabbed at the fabric in the back and gave it a tug to little effect.

"Fine?" I gave a giggle at that as Jamie tried to look over his shoulder, eyebrow raised critically but I saw nothing wrong.

"It's a bikini cut, it doesn't cover up everything in the back. These will do that." I held up the purple boy shorts and he flushed, letting the hem of his shirt down. Now he looked like a stereotypical girl getting ready for bed, wearing only a long t-shirt. Once he ditched the bra, then the image would be perfect.

Opening the bag, I picked out everything else and lay them before me, as if I was some old time merchant. Jamie took a few steps over, looking at the spread.

"'Whatta buyin'?'" I said in a gruff voice, spreading my arms wide and breaking out in a giant shit eating grin.

"Really? That's what your going with?" I threw back my head and laughed, the giddy energy of Jamie being half naked within arm's reach making me recall half remembered memes from bygone years. He picked up the plain pair of pants, looking at them thoughtfully. "I never thought I'd own a pair of chick jeans." Jamie mused, the legs unfolding as he held them up for inspection.

"'Chick jeans?'" He looked at me, not annoyed but questioningly.

"Yeah? What do you call them?" I opened my mouth but said nothing. I called them jeans but well, I was a chick. They were as normal as a bra to me.

"Good point. You now own two pairs of chicky jeans." He flushed further red at that, that small, pleased smile back. It was becoming more and more obvious that this meant something to Jamie and I was glad to be here for him. Sitting on the bed beside me, he took his time slipping legs into them, as if savoring the experience. I silently watched, grinning at the hip wiggle to get them all the way up. He had that down already.

Standing there in a Metallica shirt that depicted Lady Justice being pulled down by ropes, Jamie extended a leg and looked at it before turning his gaze to me. They were snug, molding to his thighs and yes, even clinging to his calves. Lifting up his shirt again, I saw that bump at his crotch had yet to disappear. Looking at the mirror in the corner, he examined front, side and back, not saying anything but his face burned all the while.

"We didn't buy any shirts." Looking at what lay before me, I knew that was the case but still felt disappointed that I'd overlooked that. Then again, Jamie hadn't said anything about wanting any and...

"Grab one of mine." Leaving behind the mirror with a lingering gaze I couldn't read, Jamie went to the closet and flicked the light on, disappearing inside. His shirt was tossed out and he emerged, in a black top with a lower cut neck that hinted rather that showing off everything.

Now in chick's clothing top to bottom, Jamie studied his reflection and I did the same while resisting the urge to tackle and ride him right there on the floor. He did have a nice butt that these jeans showed off better but wasn't quite there yet. Still, they did favors for his legs, showing them off nicely and one could tell there was some badonk happening in the back.

"You like 'em?" He nodded, deep in critical thought with his lips puckered slightly, that kicking my memory on. At the foot of my bed, under my coat, was the haul from earlier that would come in handy soon.

"Don't like them strangling my calves." I shrugged and he gave a sheepish smile. "I know, still weird for me."

"Just gotta wear 'em more to get used to it." Panic crossed his face but quickly passed, Jamie frowning at the mirror as I grabbed the new stuff and brought it over. Seeing Jamie like this was convincing me that he could probably pass for a girl if he wanted to but... Well, that was the question, wasn't it? What did Jamie want out of all of this? Was dressing up here enough for him? God knows we both got off on it.

"I want to try the other pair." Facing me, he smoothed the jeans over his butt, as if disappointed they weren't tighter. Which wasn't what I ever expected to see but hey, I'm not complaining!

"Wanna try another pair of underwear too?" I gestured to the goods before me and Jamie came over, the fresh pair of jeans rasping slightly as he walked. Surprising me, he picked up the soft colored pack then stared so long and intently he might have been trying to burn a hole through them.

"Hey, what's up?" I waved a hand and he returned to here and now, eyes flickering from the panties to me then the floor.

"I-These... Are really girly." I blinked a few times as Jamie floundered in trying to explain himself. "Everything else has been sexy, ah... At least to me. These are so... Normal? I guess? I never thought about wearing anything like this." Bringing them up, he looked at panties of a type and color probably every girl in America had worn at some point in her life, then at me. "I'll try them on but... It feels like it's a step too far." I snorted at that, unable to help it.

"And the push up bra or mini skirt wasn't? Or the humping?" Jamie's blush deepened as I stood, legs protesting after sitting for so long. "Look, if you don't want to wear 'em, then don't. It's fine by me."

"It's not that..." He pondered as I dug about in the newer bag, finding what I was after and tucking it in my back pocket as he spoke. "When I'm here with you, doing this, it's like there's a hand squeezing my stomach and tha-that feeling turns me on. So much. And each time I've, ah, finished with you, it's better, more intense than any I've had by myself." Practically panting after getting all that out, Jamie stood with his arms pulled before his chest, vulnerable and small. Before I could say anything, he pulled me into a hug, his breathing loud in my ear as I held him close.

"I want to, I do, but it's... I'm savoring it? Yeah, tha-" Finding his butt and grabbing hold, I kissed him, taking away what he was going to say next. I knew all about savoring this time here, each glimpse of Jamie in something outside of his normal was a treasure and me behind him, thrusting and grinding, was something I still couldn't fully comprehend.

"If those panties makes you all hot and bothered, then I wanna see what this will do." Pulling the lip gloss out of my pocket, I held it up for Jamie to examine. It was a small, clear tube with text boasting about ultra shine and 'Shimmer Pink' in large letters. Jamie looked confused but my mind was racing, goaded on by what Jamie had said. "Here, lets get you changed first." Planting a kiss on his forehead, I let loose and gestured for him to open the girly panties.

Fighting the plastic, face still burning and out of breath, he handed it over to me and slouched. Before I could even ask, he waved the question away, standing up straight and breathing deep. "I'm fine, I swear. Having the time of my life." Pulling out my car keys, I poked a hole in the wrapper and freed the panties that were causing Jamie so many problems. I pulled out the pinkest ones, tossing the others towards my bed as I ignored his outstretched hand. Having told me what turned him on, I intended to see how far I could push it and how Jamie would react.

"Stop me if it's too much." I said, taking his expecting hand and guiding it to my hips as I leaned in for a kiss. My tongue pushed into his mouth, no resistance from him as he took hold of my ass. With those bubble gum pink panties still in my hand, I caressed his face with them, a moan spilling from him to me. Down his neck and to his heaving chest, Jamie had stopped kissing me but stood there with his eyes screwed shut, breathing hard.

"Keep. Going." He couldn't see my smile at his words but I did as he asked. Running my hands down his front, I slipped them under the shirt and slid it up, exposing the peach T-shirt bra I'd given him. Holding the fabric between my fingers, I slid the panties over where Jamie's breasts swelled from the flat of his chest, breath hitching as I did so. Then down one slope and up the other as I adjusted where I stood, slipping my hand in the bra and exposing his areola to this gentle torture. A gasp was my reward as I once more moved behind him, knowing I couldn't go too far this time.

My left hand slipped down to his waist, creeping under the jeans and feeling the elastic of his panties. Undoing the button, he made a feeble mewing noise at that, I freed my other hand, the business one, from the bra and down it went.

Those pink and girly panties that Jamie seemed to think was a step too far partially disappeared down the front of his chick jeans. I felt the heat of Jamie's dick through them as I covered it from head to base, tenderly kissing the side of his neck all the while. His breath hissed, as if he was in pain but not a word about stopping had been uttered.

"Is this too far?" A whine escaped him, his penis jumping at my words. "I hope not cause you haven't even worn them yet." Leaving the panties sticking out of his jeans, I removed my hand and stepped back, Jamie stumbling forward.

Taking a few zombie like steps, he flopped face first onto my bed, laying there with his ass in the air before rolling over, revealing that slip of pink contrasting against what he was wearing. Leaving him laying there, I went digging in my dresser for something else that Jamie might be interested in once he recovered.

"Oh. That was... Oh God." Plucking the panties free, Jamie sat up enough to look at me. "I don't even know..." Still breathing hard, Jamie struggled to speak but failed to produce a noise aside from panting.

"I thought you might like it and looks like I was right." He nodded, fighting to his feet and rubbing his face. "Now pick out a pair for me so we can change." Blinking, Jamie looked at the bed and held up the other pink pair.

"Okay, what else do you want me to wear? Or is that it?" He gaped at me, looking so befuddled I had to laugh. "Fair enough, you took your pants off for me." I walked over and handed him a shirt I'd dug up, a tight pink thing with a deep neckline that was about as subtle as an erection. Taking the underwear from him and pecking a kiss on his cheek, I took my time walking to the closet, smiling as I closed the door behind me.

That I had nearly made Jamie blow his load by touching him with panties was... Empowering doesn't even begin to describe it. That I'd kept from pushing him over was a bonus, so this could keep going. Dropping my pants and swapping underwear, I looked down at the standard fair and wondered how Jamie felt pulling them on. Sure, they were a bit tight on me but this was for his benefit, not mine.

Stripping off my shirt, I hoped Jamie liked what he saw. I was still in decent shape even with eating trash since school started, not as toned as Donna but I was fine with that. Picking up my pants, I found the lip gloss and stashed it in my bra, happy I'd remembered it.

"Gen?" Opening the door, I walked out to Jamie having changed, before the mirror and averting his eyes from me. Walking over to him, the air cool on my bare skin, I joined him as I had done the night he tried on the push up bra. "I think I like these jeans more?" The first thing I'd actually noticed was the shirt was tight enough I could see the bra straps running over his shoulders and the color popped against his pale complexion.

The fancier jeans with the faded thighs fit much better and by that I mean tighter. Jamie from the waist down was clearly on display and I could tell he still was popping a boner, no chance of hiding that. I leaned back, trying to get a look at from behind and Jamie obliged my unspoken request, turning his back to me. I gave a low whistle, as there was no slack to these. His ass, with designs and patterns on the back pockets, was being shown off about as well as denim could manage. It was a Bubble Butt anyone would give a thumbs up to.

"I can see why you like them." Slipping my hands about his waist, I embraced him from the back, making him jump. "I could take a picture of dat ass and hang it on the wall." Not even a lie.

"Wouldn't Donna ask questions?" I brushed off that question as I crept a hand round front.

"Why would she care? Hers' probably got ran off in practice." Wriggling fingers back under the waistband, his breath caught as I felt that little bow on the pink panties he was now wearing. "So is this too far or do you want to keep going?"

"Gen, if you stop I'm gonna die." Circling Jamie, I caught his chin as he tried to look away.

"I got to see you like this, you get to see me." Pulling out the lip gloss, I told Jamie to watch. I wiped my lips on my arm, not very ladylike but fuck it, and painted it on. It was wet and clingy, having been a while since I'd worn it. Jamie had watched with great interest and perked up when I dipped the applier back in.

In short order I'd glossed Jamie's lips, showing him how to rub them together before he approached the mirror as if it was the Ark of the Covenant instead of his reflection. With what he was wearing and the simple addition of lip gloss, Jamie had been pushed further towards looking like a girl, the natural blush he was wearing helping. Undoing the fly of the snug as fuck jeans, he looked at the panties and shivered.

The wild look Jamie was wearing as he turned from the mirror told me everything. While I might not understand everything going on in his head, I knew this was more, further than he had ever expected. We looked at each other, Jamie finally not shying away from openly looking at me. With his women's jeans unbuttoned, showing a nearly matching shade of pink to the shirt, Jamie was a far cry from when I had first seen him. His lips, shiny and parted just so, said a single word:

"Please?"

There was no denying Jamie, not when he asked in that light voice and eyes that looked up through heavy lids. I had him in my arms within the moment and I tasted false cherry on his lips as we explored each other.

Time skipped as we made out, groping and stealing what air we could before diving back in. I kept pushing into what his jeans failed to hide, Jamie returning the gesture as we had done last time.

Gently pushing him backwards, Jamie broke from me with a startled gasp, falling backwards on my bed. A question formed on his shiny lips but I silenced him with a kiss, sinking to my knees and undoing his jeans once more. Waiting was the panties that had nearly driven him insane as I tugged more at the chick jeans, his breathing picking up at realizing what I must be after.

Teasing that last pink barrier down, that bow on the front disappeared as Jamie's sole claim to masculinity jumped free and I finally got a good look at it. While it wasn't as big as the one I'd handled before, it was thick and the word 'chub' popped in my head, fittingly enough. I smiled as Jamie spread his legs, the expression on his face closer to pain than anything approaching pleasure. Getting a hand around it, the head and a little more peeking out of the end, I gave a few tugs that made him groan.